Maybe Insanity
by SilverNight18
Summary: Wincest! Sam and Dean find a nice waitress and take her home. Better than a tip, no?


**This is a dark (ish?) fic, in which the brothers are hunters, but are in an incestuous relationship and participate in brutal threesomes with random women. Odd, I know.**

"Can I get you anything else?" the waitress asked, thrusting her breasts just inches from Sam's face as she bent over to retrieve his plate. Her nametag clearly stated that she was named Kelly. She flashed both brothers a seductive smile and Dean returned it with a casual smirk of his own.

"Well," the older Winchester said cockily, "We'd like to know when your shift is over." He cast a glance at Sam who nodded with a wicked grin.

Kelly checked her watch and smiled with full, lipsticked lips. "Now," she murmured. "Bill's on my tab!" she called back to the kitchen, and the manager poked his head out and saw the waitress pointing to the table with the two young men. He nodded.

"I'll take it off your pay," he replied before ducking back into the kitchen and yelling at the cooks.

Kelly licked her lips generously before throwing her apron onto the boys' table. "Shall we?" she asked seductively.

"Of course," Sam answered suavely. "C'mon, Dean."

A few minutes passed to find Dean fighting a raging boner as he drove through the streets of Chicago towards their motel. He kept hearing the breathy gasps of Kelly as Sam claimed her lips in the passenger seat. Dean swallowed his jealousy as the blond waitress straddled Sam and grinded her hips down on his, eliciting a sexy moan from Sam.

They pulled into the parking lot quickly and hopped out of the car, with Kelly still laving at Sam's neck as Dean fumbled at the locked door.

As soon as the door was shut, the boys' easy demeanors vanished. Dean pushed Kelly down on the king-sized bed that he shared with Sam. "Stay, bitch," he snarled, discarding his clothes as Sam did the same. Both brothers were sporting magnificent erections and Kelly licked her lips in anticipation.

Sam went to straddle Kelly's waist, his erection throbbing deliciously as he unbuttoned the blond's shirt quickly, throwing it to the side with disdain. He pressed harsh kisses to the bared skin on her chest before he got off of her and pulled her up as well, pushing her to stand in the center of the motel room.

Dean descended on her next, brutally yanking her miniskirt down her legs, leaving her only in her thong and bra. "Whore," he muttered to Sam, just loudly enough so that Kelly could hear too. "We have to teach her how to be a good girl, don't we, Sammy?"

"But of course, Dean," Sam answered slyly, grinding against Kelly's ass as he unstrapped her bra and let it fall to the floor, exposing her already hardened nipples. Dean made short work of the skimpy thong, using his pocketknife to cut through the hair-thin straps and let the little triangle of fabric fall to the ground, leaving Kelly naked in the center of the room. "Dean," Sam ordered, "get the stuff." Meanwhile, he reached his fingers towards her core, stroking along the flesh between her legs and tutting when he found dryness. "That needs to change," he reprimanded, unceremoniously shoving his fingers into her, playing along her walls as she bit her lip around the pressure that formed as her body eagerly responded to Sam's encouragements. Sam drew his fingers out slowly, looking approvingly at the warm wetness he found there. "Perfect," he hissed in her ear, biting her earlobe viciously.

Dean disappeared into the motel's closet, emerging with a cushioned ottoman, nipple clamps, and something that looked suspiciously like a vibrator to Kelly. "Here you go," Dean growled, setting the ottoman down and putting the other supplies on the bed. "Kneel on that," he ordered Kelly, and the waitress obliged, nearly trembling in anticipation. Dean moved to recline on the bed. "You can go first, Sammy," he offered. "I'm perfectly content to watch."

Sam nodded and came up behind Kelly, lifting her ass slightly and kneeling behind her so that her legs were spread and his were in between them. His aching member pushed at the entrance to her wet and pulsing depths, and Kelly moaned loudly as Sam pulled her into his lap, penetrating her deeply. Sam sat for a moment, savoring the feel of the waitress's walls periodically clenching and caressing his dick. Then, without removing himself from Kelly's depths, Sam grabbed the blond's hips and pulled her back with him as he moved to stand right behind the ottoman. He moved Kelly to her hands and knees and slowly drew himself out of the girl's dripping pussy, so that only the tip was throbbing inside Kelly. The blond whined in protest as she was emptied, bucking backwards in an attempt to get Sam's cock back into her. Sam grabbed her hair and slapped her.

"You don't move unless I say so," he snarled, looking over at Dean, who was watching the exchange with blackened eyes, his hand playing along the length of his own swollen member. When the older hunter nodded approvingly, Sam grabbed Kelly's hips so hard that they would surely leave bruises, bringing them backward as he slammed back into the girl's eager and welcoming depths, groaning as he buried himself balls-deep inside her. Kelly screamed her pleasure, her moans hitching as they were interrupted by Sam's brutal thrusts.

Dean could take it no longer. After watching Sam bend over the girl's back to bite at her spine and fondle her shaking breasts, making her scream as he played and pinched at her nipples, the older hunter hopped off the bed and grabbed the vibrator from the foot of the bed. Sam looked over and his already dark eyes turned black with lust as he saw his brother approaching with his dick hard and oozing. The shaggy-haired man, still thrusting into Kelly, focused on his brother. He unceremoniously yanked his swollen cock from Kelly, ignoring her moans of protest and leaving her to thrust her fingers inside herself to sate herself in his absence. He paid no attention to her gasps and moans, focusing only on his brother, who grabbed Sam and pulled him down for a punishing kiss.

The brothers attacked each others' mouths, their tongues battling for dominance as they ground their dripping cocks against each other, desperate for friction. Kelly paused in her pleasuring of herself and looked behind herself, eyes widening as she saw the two men so passionately embracing. She watched in awe as Sam forced Dean facedown onto the bed, grabbing the vibrator from the short-haired man's hand. He grabbed some lube from where he'd stashed it underneath the pillow and generously lubricated the vibrator before slowly pushing it into Dean's ass. The older hunter groaned into the blankets, squirming and hissing out his pleasure. Sam grinned and turned the vibrator on to full intensity, watching as Dean writhed on the bed. He pulled his brother - lover? Kelly wondered - off the bed and pulled him over to Kelly.

"Back to your hands and knees," Sam ordered, waiting as she did so. He lined himself up again with her entrance and pushed in with a satisfied groan, grabbing the nipple clamps from the ottoman and clipping them onto Kelly's swollen breasts, smiling cruelly when she bucked against his cock, hissing in pain. Once Sam was situated nicely in Kelly's shaking body, he beckoned Dean over and nodded, an unspoken agreement passing through their eyes.

Dean grabbed Sam's hips and thrust into his ass in a single, merciless push.

Sam nearly screamed and thrusted brutally into Kelly as Dean did into him, pulling out as his brother did the same.

Dean was in a whirlwind of pleasure, receiving it from both ends. The vibrator was pulsing violently against his prostate, nearly making his vision black out from the pleasure, not to mention the sensations he got from pushing into his Sammy's tight and welcoming ass.

Kelly had long since stopped any logical thought and was balancing on one hand as she used her left one to stroke her throbbing clit, desperate for release from the pressure building in her abdomen. All coherent thoughts that passed through her head were roughly translated into garbled moans, screams, and groans of "More, Sam!"

The first one to come was Kelly, screaming in ecstacy as her body bucked against Sam's turgid member, coating his cock with the results of her pleasure. Ignoring the fact that his partner was spent, Sam continued to pound away at her drenched depths, growling when he no longer found her to be tight enough. He yanked his dick out of her, groaning when Dean's dick hit his prostate, and brutally fucked into Kelly's ass, lubricating her entrance with her own come. The blond screamed when he stretched her oversensitized opening, and her jaw lolled laxly.

Dean was next, overwhelmed by the feelings of pleasure coursing through him. Biting down on Sam's muscled back, he growled out his orgasm, still thrusting into his brother while spilling his come into his ass, filling him. He pulled out slowly and watched with satisfaction as his seed dripped out of his brother's ass.

Sam, having endured ages of relentless thrusting from himself and Dean, screamed hoarsely as he came as well, bending over to slump over Kelly's body. The blond had fallen into unconsciousness, and Sam pulled out of her ass quickly, turning away from her with a glance of disdain. He scooped Dean up in his arms, bridal style, and carried him to the bed. They fell onto the mattress together, exchanging languid kisses.

"Take it out?" Dean asked.

Sam nodded and pulled the vibrator out of Dean's body, turning it off and tossing it to the side carelessly. He pulled the shorter man flush against his body, sighing happily at the feeling of wholeness. "That was interesting," he commented.

"Next time, Sammy," Dean drawled, "I get to fuck the chick."

"Or we can forgo the chick entirely and have you fuck me into the mattress over and over," Sam suggested.

Dean smirked. "I can work with that."


End file.
